000119885 001__ 119885
000119885 005__ 20240319081014.0
000119885 0247_ $$2doi$$a10.1021/acs.joc.2c01956
000119885 0248_ $$2sideral$$a130586
000119885 037__ $$aART-2022-130586
000119885 041__ $$aeng
000119885 100__ $$aLassfolk, Robert
000119885 245__ $$aAcetyl Group Migration in Xylan and Glucan Model Compounds as Studied by Experimental and Computational Methods
000119885 260__ $$c2022
000119885 5060_ $$aAccess copy available to the general public$$fUnrestricted
000119885 5203_ $$aIt was recently demonstrated by us that acetyl groups in oligosaccharides can migrate not only within one saccharide unit but also between two different saccharide units. Kinetics of this phenomenon were previously investigated in both mannan model compounds and a naturally occurring polysaccharide. In addition to mannans, there are also several other naturally acetylated polysaccharides, such as xyloglucans and xylans. Both xyloglucans and xylans are some of the most common acetylated polysaccharides in nature, displaying important roles in the plant cells. Considering the various biological roles of natural polysaccharides, it could be hypothesized that the intramolecular migration of acetyl groups might also be associated with regulation of the biological activity of polysaccharides in nature. Consequently, a better understanding of the overall migration phenomenon across the glycosidic bonds could help to understand the potential role of such migrations in the context of the biological activity of polysaccharides. Here, we present a detailed investigation on acetyl group migration in the synthesized xylan and glucan trisaccharide model compounds by a combination of experimental and computational methods, showing that the migration between the saccharide units proceeds from a secondary hydroxyl group of one saccharide unit toward a primary hydroxyl group of the other unit.
000119885 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E34-20R$$9info:eu-repo/grantAgreement/ES/MICIU/PID2019-104090RB-100
000119885 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000119885 590__ $$a3.6$$b2022
000119885 592__ $$a0.892$$b2022
000119885 591__ $$aCHEMISTRY, ORGANIC$$b10 / 52 = 0.192$$c2022$$dQ1$$eT1
000119885 593__ $$aOrganic Chemistry$$c2022$$dQ1
000119885 594__ $$a6.8$$b2022
000119885 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000119885 700__ $$0(orcid)0000-0003-4249-6748$$aPedrón, Manuel$$uUniversidad de Zaragoza
000119885 700__ $$0(orcid)0000-0003-3433-6701$$aTejero, Tomás$$uUniversidad de Zaragoza
000119885 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, Pedro$$uUniversidad de Zaragoza
000119885 700__ $$aWärnå, Johan
000119885 700__ $$aLeino, Reko
000119885 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000119885 773__ $$g87, 21 (2022), 14544-14554$$pJ. org. chem.$$tJournal of Organic Chemistry$$x0022-3263
000119885 8564_ $$s3387196$$uhttps://zaguan.unizar.es/record/119885/files/texto_completo.pdf$$yVersión publicada
000119885 8564_ $$s2605894$$uhttps://zaguan.unizar.es/record/119885/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000119885 909CO $$ooai:zaguan.unizar.es:119885$$particulos$$pdriver
000119885 951__ $$a2024-03-18-15:29:53
000119885 980__ $$aARTICLE